Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (4-Methoxyphenyl)boronic acid | HCID 201262 | — |
| Reactant | Bis[2-(diphenylphosphino)phenyl] ether | HCID 4285986 | — |
| Reactant | 3-Bromo-8-(methylsulfanyl)imidazo[1,2-a]pyrazine | HCID 57803107 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58337131 | HCID 58337131 | 85.1% |
Reaction Steps
A mixture of 3-Bromo-8-methylsulfanyl-imidazo[1,2-a]pyrazine (1.06 g, 4.33 mmol), 4-methoxybenzeneboronic acid (0.79 g, 5.2 mmol), Pd(OAc)2 (0.05 g, 0.22 mmol), (oxidi-2,1-phenylene)bis(diphenylphosphine) (233 mg, 0.43 mmol), 1.5M K2CO3 in water (5.8 mL, 8.66 mmol) and DMF (12.8 mL) is stirred at 88° C. for 16 h. Then allowed to cool, filtered through cotton, diluted with EtOAc and washed with water and brine. The organic layer is dried with MgSO4 anh., filtered and evaporated. The crude is purified by column chromatography using a gradient of (Pet. Ether 40-60/AcOEt: 7/3 to 1/1) to give 3-(4-Methoxy-phenyl)-8-methylsulfanyl-imidazo[1,2-a]pyrazine as a pale yellow solid (1.0 g, 85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08362018B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-0187456a0bf84461b855ac6173c31a74 |
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| Source note | uspto-grants-2013_01 |
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